4-Toluenesulfonyl chloride → 2,2-Dimethyl-3-[2-(4-toluenesulfonyloxy)ethyl]-chroman

HRID 1032429

Reaktionsgleichung

Reaktionsgleichung von HRID 1032429
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]1([CH3:26])[CH:22]([CH2:23][CH2:24][OH:25])[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14]1>N1C=CC=CC=1>[CH3:12][C:13]1([CH3:26])[CH:22]([CH2:23][CH2:24][O:25][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14]1

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 545643192,2-Dimethyl-3-(2-hydroxyethyl)-chroman

Produkt 1

HCID 540378412,2-Dimethyl-3-[2-(4-toluenesulfonyloxy)ethyl]-chroman

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

38 g (0.2 mol) of 4-toluenesulfonyl chloride are added at room temperature, while stirring, to a solution of 37.1 g (0.18 mol) of 2,2-dimethyl-3-(2-hydroxyethyl)-chroman in 150 ml of pyridine, the slightly exothermic reaction being maintained at room temperature with an ice bath. The mixture is then stirred for 4 hours at room temperature. The reaction mixture is then poured onto ice-water and extracted with diethyl ether. The combined ethereal phases are washed three times using 150 ml of citric acid solution (5%) each time and three times using 150 ml of water each time, then dried over sodium sulfate and concentrated by evaporation, yielding 59.1 g (89% of the theoretical yield) of 2,2-dimethyl-3-[2-(4-toluenesulfonyloxy)-ethyl]-chroman in the form of a yellow oil which is further used in that form.

Aufarbeitung

  1. customthe slightly exothermic reaction
  2. additionThe reaction mixture is then poured onto ice-water
  3. extractionextracted with diethyl ether
  4. washThe combined ethereal phases are washed three times
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customyielding 59.1 g (89% of the

Quellen und Nachweise

ORD-Eintrag
ord-002930fa073f4aac8dd8ce6edd2762c3
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04957928

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